In Tobias Wolff's Old School, Dean Makepeace resigns because of a guilty conscience. For years, the Dean does not dismiss the impression that he knows the famous writer, Ernest Hemingway.This impression is formed by the general student population at his school after he neglected to correct certain implied assumptions. Although both Dean Makepeace and Ernest Hemingway sustained injuries to their legs during their service in the war, both worked for different organizations. The Dean served with the Army Ambulance Service, while Hemingway worked with the Red Cross. As such, they never crossed paths.
Because of his pronounced limp and implied association with Hemingway, the Dean has always been treated with great respect by the entire student population. However, he never corrects the students' assumptions. Years later, he recognizes that his reticence stemmed in part from 'some hidden yearning to be part of the great world. To be important, even by association.' When the unnamed narrator is expelled for plagiarism, Dean Makepeace decides to resign. He confesses that he himself has broken the Honor Code for years and that he cannot bear to continue as dean while a boy is expelled for a similar crime.
Although Dean Makepeace classes Hawthorne among his favorite authors, he is not above succumbing to the same mental anguish endured by some of Hawthorne's flawed protagonists. Ironically, he both enjoys and feels oppressed by stories such as 'The Minister's Black Veil.' Eventually, it is Dean Makepeace's inability to appreciate Hawthorne's warning against an obsessive preoccupation with purity which causes him to resign.
Through story after story, he'd led his boys to consider the folly of obsession with purity- its roots sunk deep in pride, flowering in condemnation and violence against others and oneself. For years, Arch had traced this vision of the evil done through intolerance of the flawed and ambiguous, but he had not taken the lesson to heart. He had given up the good in his life because a fault ran through it. He was no better than Aylmer, murdering his beautiful wife to rid her of a birthmark.
After much cogitation, Dean Makepeace comes to the realization that he made a mistake in resigning. He is welcomed back to the school by the headmaster, who wisely records his former employee's period of absenteeism as a leave. Yet, the Dean finds that his rash decision to resign means that his relationship with the headmaster will never resort to its former, easy camaraderie. In order to teach at the school once more, he has to promise never to allude to the truth about his relationship with Hemingway and to relinquish his former position as dean. Hawthorne's teaching that austere intolerance always leads to great suffering and regret comes true in Dean Makepeace's life.